You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:58:46 UTC
Update Date2018-05-20 20:27:38 UTC
HMDB IDHMDB0060387
Secondary Accession Numbers
  • HMDB60387
Metabolite Identification
Common Name4-Glutathionyl cyclophosphamide
Description4-Glutathionyl cyclophosphamide is a metabolite of cyclophosphamide. Cyclophosphamide ( trade names Endoxan, Cytoxan, Neosar, Procytox, Revimmune), also known as cytophosphane, is a nitrogen mustard alkylating agent, from the oxazophorines group. An alkylating agent adds an alkyl group (CnH2n+1) to DNA. It attaches the alkyl group to the guanine base of DNA, at the number 7 nitrogen atom of the imidazole ring. It is used to treat various types of cancer and some autoimmune disorders. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H30Cl2N5O8PS
Average Molecular Weight566.394
Monoisotopic Molecular Weight565.092975577
IUPAC Name2-amino-4-{[2-({2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2λ⁵-oxazaphosphinan-4-yl}sulfanyl)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional NameC17H30cl2N5O8PS
CAS Registry NumberNot Available
SMILES
NC(CCC(O)=NC(CSC1CCOP(=O)(N1)N(CCCl)CCCl)C(O)=NCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C17H30Cl2N5O8PS/c18-4-6-24(7-5-19)33(31)23-14(3-8-32-33)34-10-12(16(28)21-9-15(26)27)22-13(25)2-1-11(20)17(29)30/h11-12,14H,1-10,20H2,(H,21,28)(H,22,25)(H,23,31)(H,26,27)(H,29,30)
InChI KeyCXEDBYAXQXFDHD-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha peptide
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Nitrogen mustard
  • Phosphoric monoester diamide
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxazaphosphinane
  • Fatty acyl
  • Organic phosphoric acid amide
  • Fatty acid
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Organoheterocyclic compound
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Organonitrogen compound
  • Alkyl halide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Alkyl chloride
  • Primary amine
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organosulfur compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Organochloride
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP-1.7ALOGPS
logP-2.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area207.37 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity125.88 m³·mol⁻¹ChemAxon
Polarizability52.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9440780000-72a130ffdc0663407ea5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06y6-5051192000-85c6673bb5eb4869b5f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-3139020000-046b94793b5ffdc91fefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9724100000-8aaf34c2e69014649e08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9130000000-3b7c56c19d5091ab9e50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zgj-0212590000-d3604655628d2a5897dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9016000000-bf78140826d14fe805c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9841000000-f940fa82fb8f8898fd89View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC11583
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound443288
      PDB IDNot Available
      ChEBI ID1831
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      Only showing the first 10 proteins. There are 19 proteins in total.

      Enzymes

      General function:
      Involved in glutathione transferase activity
      Specific function:
      Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
      Gene Name:
      GSTM2
      Uniprot ID:
      P28161
      Molecular weight:
      25744.395
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in glutathione transferase activity
      Specific function:
      Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
      Gene Name:
      GSTM1
      Uniprot ID:
      P09488
      Molecular weight:
      25711.555
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in protein disulfide oxidoreductase activity
      Specific function:
      Significant glutathione conjugating activity is found only with the model substrate, 1-chloro-2,4-dinitrobenzene (CDNB).
      Gene Name:
      GSTK1
      Uniprot ID:
      Q9Y2Q3
      Molecular weight:
      31565.605
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in glutathione transferase activity
      Specific function:
      Also functions as a glutathione peroxidase.
      Gene Name:
      MGST3
      Uniprot ID:
      O14880
      Molecular weight:
      16516.185
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in glutathione transferase activity
      Specific function:
      Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May govern uptake and detoxification of both endogenous compounds and xenobiotics at the testis and brain blood barriers.
      Gene Name:
      GSTM3
      Uniprot ID:
      P21266
      Molecular weight:
      26559.32
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in glutathione transferase activity
      Specific function:
      Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
      Gene Name:
      GSTA1
      Uniprot ID:
      P08263
      Molecular weight:
      25630.785
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in glutathione transferase activity
      Specific function:
      Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a wide substrate specificity.
      Gene Name:
      MGST1
      Uniprot ID:
      P10620
      Molecular weight:
      17598.45
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in glutathione transferase activity
      Specific function:
      Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
      Gene Name:
      GSTM4
      Uniprot ID:
      Q03013
      Molecular weight:
      25561.095
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in glutathione transferase activity
      Specific function:
      Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
      Gene Name:
      GSTM5
      Uniprot ID:
      P46439
      Molecular weight:
      25674.455
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails
      General function:
      Involved in enzyme activator activity
      Specific function:
      Can catalyze the production of LTC4 from LTA4 and reduced glutathione. Can catalyze the conjugation of 1-chloro-2,4-dinitrobenzene with reduced glutathione.
      Gene Name:
      MGST2
      Uniprot ID:
      Q99735
      Molecular weight:
      16620.4
      Reactions
      Aldophosphamide + Glutathione → 4-Glutathionyl cyclophosphamide + Waterdetails

      Only showing the first 10 proteins. There are 19 proteins in total.